


Pleasurable Revenge

by thewinchesterlifestyle



Category: Supernatural
Genre: Age Difference, Barebacking, Begging Dean, Bondage, Bottom Castiel, Castiel and Dean Winchester are Roommates, Cock Cages, Cock Rings, Cock Slut Castiel, College Student Castiel, Dildos, Dirty Talk, Dorms, Fingering, Gags, Loud Sex, M/M, Multi, Name-Calling, Not within a bdsm setting, Objectification, Orgasm Delay/Denial, Orgasm Denial, Restraints, Revenge Sex, Riding, Roommates, Rough Sex, Size Difference, Size Kink, Slut Castiel, Smut, Submissive Castiel, Threesome, Top Dean Winchester, Twink Castiel, Twink Dean Winchester
Language: English
Status: Completed
Published: 2018-05-27
Updated: 2018-07-24
Packaged: 2019-05-14 06:57:10
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,639
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14764788
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: Castiel is tired of listening to Dean bringing back one-night-stands every single night and keeping him awake listening to his roommate having loud sex. He's more than happy to give Dean a taste of his own medicine.





	1. Chapter 1

**Author's Note:**

> Written for a prompt.

There was only so much of it he could take. Every single night his roommate would go out, pick someone up and come back to have loud, annoying sex and Castiel would _have_ to put on headphones if he wanted any hope of sleep.

He had been _trying_ to be a considerate roommate, to keep his own activities to respectable times and with consideration to Dean’s schedule, but after the _tenth fucking night in a row_ Castiel had reached his breaking point. What was the point in being respectful if his roommate couldn’t be bothered?

If Dean wanted to go out, pick someone up and have headboard banging sex when Castiel was trying to sleep without a single care then why should he hold back? Why shouldn’t Castiel return the favor?

He’d been known as the town bicycle the second he’d discovered sex and it had continued through his entire high school career. Castiel had started young, in a house full of horny older brothers it couldn’t have been a surprise, and he’d discovered how much he _loved_ being fucked. By the time he’d graduated he had already lost track of how many different guys he’d let fuck him and his virginity had been long gone.

Now he lived in a city, a city with a population in the _millions_ , and there were plenty of potential one-night-stands he could bring back for a good time all the while showing Dean exactly how it felt.

Castiel didn’t even have to try.

He was in the bar less than ten minutes before he was propositioned by _two_ big, burly guys who looked like they could break him in half. All it took was a glance down at their pants and he could actually _see_ the outlines of thick, long cocks that Castiel _knew_ would feel perfect splitting his ass open. The very thought of an enjoyable night that didn’t end with him listening to Dean fucking a one-night-stand had him practically shaking with excitement. As they left the bar he tried to remember the names they had given him but shrugged it off. It wasn’t as though it mattered. Castiel only wanted them for loud, enthusiastic and kinky sex.

Both followed him back to his dorm suite, Dean wouldn’t be back from his late class yet, and Castiel preened at the looks he was getting. There were plenty of appraising and interested looks but Castiel paid them no mind. For the moment. They could be used later to drive Dean insane if he didn’t want to go too far to find someone up for loud, wild sex.

He led both men into the suite he shared with Dean, stripping as he walked towards his room, while they followed along. No sooner had he opened his door were they on him. Castiel went limp, submissive and happily pliant in their hold. Considering the filthy promises they had made when they had first approached he was looking forward to whatever they planned to do with him.

“I want you to fuck me so hard the people two floors up can hear me screaming.”

They were naked in record time, pressing him into his mattress, while biting and licking and sucking as he writhed under them. It felt good, two warm bodies pinning him down and easily dwarfing him with their impressive bulk, as they played him like an instrument.

Castiel pushed up into them, moaning and whining, when his arousal built and his body heated with need.

He relished them manhandling him, one of them pulling him into their lap before splaying his legs wide to expose his tight ass, so they could prepare him. Thick, rough fingers coated in lube plunged into his dry hole causing him to wail loudly at the intrusion.

The man, it might have been Will, didn’t waste a moment as he started to finger fuck Castiel while the other man held him in place, kept his legs spread, so they could get him ready for the mouthwateringly big cocks both possessed.

_My ass is going to be **ruined**._

The thought filled him with nothing but aroused glee. Each finger added had him jerking and shoving into them, trying to take the fingers deeper, before one brushed against his prostate and his moan echoed in the room. His hole clenched and his cheeks flushed darker as his arousal built.

“There it is.” The man grinned, scruffy face flushed and eyes heated, as he rubbed and rubbed against that spot until Castiel was sobbing with need and begging breathlessly for release. “Ready for my dick? Such a greedy little whore looking for two men to show you where you belong?”

“Yes! Please please please please.” He was babbling but Castiel didn’t fucking care. He needed to be full and he needed to be getting fucked into the mattress right fucking now. As though hearing those thoughts the fingers fucking him open slipped out and the whine that escaped at their loss earned twin chuckles.

“He really is eager for it. Little slut has probably been gagging to be fucked full.”

They manhandled him again, shoving him to his knees and pressing his face into the mattress, as Castiel eagerly let them position him. It would mean he was full sooner and that was what mattered.

Strong hands spread his knees out wide and shoved him until his back was bowed perfectly, ass raised and fingers clenched in the sheets near where his face had been shoved.

The creaking groan of the mattress had anticipation flying through him as one of the men moved up behind him, knees braced inside of Castiel’s to force them wider until he was whining in pain at the stretch, before the fat head of a cock pushed against him.

There was no easy pace, no gentle touches, as the man fucked that gigantic cock inside of Castiel with nothing short of greed. It was the kind of fuck that Castiel expected, hoped for because he loved mixing pain with his pleasure, when he went to a bar and the harsh burn of his ass spreading wider than it had been prepared for had him choking.

“Fuck that slut. Get that hole ready for me.”

Castiel keened at the feeling of his ass being forced wide as that thick cock fucked deeper and deeper until it was fully buried inside of him and Castiel was panting against the sheets. His eyes burned at the painful pleasure, his cock gone soft where it hung neglected, as fingers knotted in his hair and a thick hand gripped his hip for leverage.

Then the man was _pounding_ into him. It was hard, fast, rough and near violent as Castiel’s body jerked from the force. Over the sounds of grunts, groans and the slap of skin Castiel could hear the protesting creak of the mattress and the loud banging of the headboard against the wall.

“That’s it! Use that ass.”

“Take it, whore, take my dick.”

Castiel would have made a comment that he was doing exactly that but all he could do was moan loudly and keen almost brokenly each time that cock nailed his prostate.

It was loud, filthy and there wasn’t a question that anyone with ears could hear them. Castiel hadn’t even heard the suite door open and shut until the other man snickered. “Think your roommate’s back.” But that wasn’t going to stop Castiel and he hoped Dean enjoyed being kept up.

Especially since Dean had a very early test in the morning and he’d planned to actually sleep tonight. It served him right.

Castiel made sure his moans were louder and louder as he was roughly pounded into. Heavy balls slapped against him with each thrust that drove the man fucking him balls deep, slamming his hips hard up against Castiel, as he chased his first orgasm. It was bliss. Pure, undeniable bliss. He let the pleasure of a good, hard fuck and the filthy dirty talk send him spiraling in pleasure.

It helped that he knew Dean wasn’t going to be getting any sleep. The same way Castiel had suffered multiple times despite his comments about Dean, maybe, keeping it down.

Finally, with a hard thrust, his current partner came with a loud groan as his hips jerked forward. Castiel’s ass clenched down, his body right there on the edge of orgasm, only for a hand to reach under and hold him off.

“You’re coming on a dick or not at all, little whore.”

The softening cock in him slipped out, sliding against his puffy rim, before it was being replaced with another blissfully thick cock. His second cock of the night slammed in without an ounce of ceremony and little resistance after Castiel’s ass had been fucked open, sloppy and ready. Castiel barely registered the sounds of his roommate moving around in the next room.

He could hear a muffled swear of _Fucking Hell…again? Already?_ as guy number two started fucking into him. It was just as rough, selfish and greedy as the first guy. Castiel shoved back, clenching down and groaned in the most filthy, needy sounding voice that he could.

It seemed his second partner had decided he was going to top the first. Fingers dug viciously into Castiel’s hips and yanked him back into each powerful thrust. Castiel yanked at the sheets as pleasure burst inside of him. Every other thrust seemed angled to nail his prostate and Castiel couldn’t stop the tumble of sound pouring out of him.

Castiel was being loud enough to compete with the loud, banging slam of the headboard against the wall and the creaking of the mattress. Skin slapped against skin, his ass aching and burning, as his toes curled and his mouth fell open.

He couldn’t have formed a cohesive though if his life had depended on it and that was exactly what he’d needed.

The sounds of fucking echoed in his room and, without a doubt, through the suite and out into the hall. He ended up coming, completely untouched, with a loud keening wail that only seemed to drive the man inside his ass even more. Every single thrust after that had his sensitive body shuddering and hitching little sobs escaped into the air.

A second load was emptied into his ass before the soft cock slipped free.

“Hell of a fuck.” The praise washed over him as he collapsed onto the sheets, come and lube leaking out of his fucked open hole. He could only groan when fingers pushed into his used ass, finger fucking him, as he twitched and his cheeks flushed. A low, broken sounding whimper escaped as the fingers inside of him spread wide. “Look at that little ruined hole.”

“We wrecked that sweet ass.”

“You have any toys?”

Castiel managed a rough _under the bed_ as fingers curled in his hair and yanked the same time fingers rubbed against his prostate. The sound of his toy chest being dragged out, opened and looked through didn’t even register as he moaned loudly at the stimulation.

The disappearance of the fingers did register. Castiel shuddered and looked over to see his biggest toy laid next to his face. He was turned, a cockcage locked onto his cock and a band around his balls, and then he was once more on his belly.

“Make sure you lube that ass.” A hand braced on his lower back and the end of his lube bottle was literally shoved into his ass before cold liquid poured into him causing him to jerk. “There we go.”

He clenched and squirmed at the feeling of cold, slick lube sliding deeper inside. The bottle disappeared shortly after and his toy was lifted to push into him. It burned and burned as the toy spread him wider and wider with each inch that sunk inside.

“Look at that greedily little hole.” the dildo fucked in deeper and deeper as Castiel shoved his face against the mattress with a cry. “He’s going to take the whole thing.”

Castiel’s ass clenched instinctively as they paused, the toy only half way inside, before rolling him over. Once again one of the men held his legs wide and the other leaned forward. He moaned, head shoved back, as the toy was fucked into him again and another few inches disappeared.

It only took a glance down to show how the horse cock sized dildo was splitting his ass. More and more pushed in, until he had taken the entire toy and a hand brushing against his stomach had them whistling.

“Holy shit. You can see it through his stomach.”

“The second I saw it I _had_ to see this slut take the whole thing.”

Castiel whimpered as fingers stroked the toy through him and it was slowly pulled out, inch by agonizing inch, before being fucked back in.

In and out.

In and out.

The giant dildo fucked deep with each thrust and Castiel moaned louder and louder, body heating and face flushed, as they commented on what a good whore he was, how greedy his hole was to be filled and how they couldn’t wait to fuck right back into him.

By the time they were ready for another round Castiel was begging and begging for release but the cage trapping him wasn’t coming off and the toy was slowly slipping from him until his gaping hole was on display.

“You’re going to ride me, slut, and then Luke is going to bend you over the bed so he can pound that sweet ass of yours.”

Castiel’s legs were shaking by the time he was straddling the man laid out on the bed, sinking down onto his cock and whimpering at the need to come. “Please… _please_ —”

“After we’re finished and only if you’ve earned it.”

Castiel immediately started rocking his hips, desperate and needy, as he fucked himself down on the cock impaling him. A hand smacked his ass causing him to jolt, a choked whine escaping, before he was moving faster and faster.

“That’s it. Show us how much you want to come.”

His legs worked as fast as he could, a hand braced on a firm chest, as the mattress started to groan lowly and the headboard knocked against the wall at an increasing tempo. In Dean’s bedroom, the same room that set right against his wall, he could _hear_ Dean cursing loudly.

The sound of his roommate’s frustration had him moving faster and faster, moaning loudly, as a large hand continued to smack against him to urge him on.


	2. Chapter 2

**Notes for the Chapter:**

> Since you're all so lovely and wanted more. Here it is!

Castiel felt so good. Constantly pleased, sated and content. He couldn’t even remember _why_ he’d been holding back. There were so many gorgeous guys on campus and so many more men in the city compared to his home town. Back home he’d been known as the town bicycle and Castiel was well on his way to becoming the campus/city bicycle. It was a silent goal that he was happily working his way to achieving. He had taken to enthusiastically fucking his way through his dorm, through campus and through the male population in the city. Sex clubs, gloryholes and bars were a great help in finding men eager to fuck him.

The whole time Castiel was bouncing from cock to cock he never made a move towards Dean.

He never showed any interest in his roommate.

Every single night he made sure to bring one or two guys back to his room where they would spend _hours_ fucking loudly even when he’d spent hours before indulging in sex elsewhere. It was nice to give Dean a taste of his own medicine _and_ to bask in the sated pleasure of regular sex.

Until tonight.

Dean had openly propositioned him, promising him that he could give Castiel something all of those others couldn’t. How could Castiel resist _that_ kind of opportunity? He could see what all of those others had been moaning about _and_ he could get off before going out to find someone else to enjoy. It was gloryhole night and he knew he afterwards it wouldn’t be hard to find someone to bring back.

The whole thing really was a win-win for him.

Castiel finished tying Dean’s arms to the headboard, testing the restraints, before checking the ones around Dean’s ankles. His roommate was spread-eagle, on his back, and completely naked. A cockring rested snugly against the base of his cock that jutted up, hard and dark colored, as Castiel grinned at him.

“Close your eyes.”

Dean looked aroused and curious but he didn’t hesitate to close his eyes. Castiel gripped the ball-gag he’d brought into the room while leaning forward to press their lips together. His ass pressed against Dean’s hard cock and earned a choked moan that had Dean’s mouth dropping open.

In seconds he’d broken the kiss and pressed the ball-gag into Dean’s open mouth.

“Fuck, Dean.” He rolled his hips back and ground himself against Dean’s cock with a groan. Dean moaned into the ball-gag as Castiel finished hooking it behind his head. “You’re going to feel so good in my ass.”

Castiel grinned as he made sure to add a few pillows under Dean’s head for the next part. That finished Castiel shifted so his ass was angled towards Dean’s face, lubed up his fingers and started fingering himself open where Dean could only watch silently. Castiel moaned throatily, finger fucking himself loose, right in Dean’s eye line as he panted with mounting bliss. He made sure to brush against his prostate, hole clenching as pleasure shot through him, until he was taking three fingers easily.

“ _Ohhhhh_.” He moaned and spread his fingers, pressed them down, before slipping them out only to feel upsettingly empty. Castiel’s cheeks were flushed, his cock hard and aching, as he spread his cheeks wide to show off his lube wet and loosened hole for Dean’s eyes to feast on. “Look at how empty I am…loose and wet and ready to take a nice, thick cock in my slutty hole.” He clenched and listened to Dean groan, “Do you want to fuck me, Dean? Want to bury that big cock of yours in my greedy ass? Give me a reason to moan and cry?”

The sounds Dean was making in response were very obviously in the affirmative. He could _see_ that Dean was still painfully hard and drooling at the tip.

Castiel smirked.

Someone was _very_ eager to fuck his ass and Castiel couldn’t wait. Dean certainly wasn’t small. He was long and thick, curling to the left, with a heavy set of balls that Castiel _knew_ would feel great smacking against his ass _if_ he let Dean take him from behind.

All things he really looked for in a top even if Dean was far from the biggest and thickest he’d taken. Castiel had sampled a very large number of cocks, greedy for a good fucking since his first cock in his early teens. Dean was going to be just another cock in a long line of cocks but he was hardly going to turn down a test drive.

Dean’s partners seemed to enjoy themselves and Castiel was sure he’d feel at least some moderate satisfaction. If nothing else he’d get pure enjoyment out of Dean begging him for release as he used him like a dildo.

“Are you going to fill my slutty hole? Leave me aching?”

Castiel was pretty sure at this point Dean would have promised him his first born just to bury himself balls deep in Castiel’s lube slick ass. He grinned, stroked his sensitive rim lazily, before letting go of his ass and moving. Dean’s eyes were dark, his pupils blown to the point there was only a thin line of green, and Dean’s freckled cheeks were flushed darkly with arousal.

“Someone looks like they need a nice, round ass to fuck into. A warm, wet hole to bury your aching cock in until you can fuck till you come.”

Dean yanked at his restraints as Castiel moved to straddle him, shifting up so his lubed ass was pressed to Dean’s stomach, before he lifted up and reached back to pick up Dean’s hard cock. He guided it to press up against his loosened asshole and pushed down onto it. The fat head popped past his rim, past the tight ring of muscle inside of him, before Castiel started to actively sink down on it.

He watched how Dean’s head pushed back, eyes rolling with pleasure, as his roommate moaned into his gag with each inch Castiel took into his warm ass.

The power had him flushing, his eyes hooding with satisfaction, as Dean’s cock spread his ass and filled him up. It felt so good to have a cock buried in his ass. Castiel wished it was possible to spend his existence being fucked but it wasn’t feasible. Fortunately the wait between rounds made the actual fucking that much more enjoyable as anticipation built in the in-between time.

Castiel moaned his enjoyment, taking more of Dean inside, until his ass settled against Dean and he was blissfully full.

“You feel so good, Dean.” He rolled his hips and clenched down, groaning, as Dean’s hips jerked up trying to fuck himself deeper despite the fact that Castiel had every inch already inside. He ground himself down, clenching tighter and swiveling his hips, as Dean swore into his gag and moaned with clear pleasure.

Castiel gave it a few more moments, savoring the feeling of full and the ache of being spread wide, before he started moving. He fucked himself vigorously down on Dean’s cock, riding him hard and rough and fast, as the mattress creaked and groaned with the power behind each movement of his hips.

He rode Dean into the mattress like his roommate was nothing more than a warm, living dildo that Castiel was using purely for his own pleasure as he prepared himself for a night of fucking.

Under him Dean tried jerking his hips up to fuck into Castiel’s ass, his muscles trembled and the muffled moans spoke loudly of how much Dean was enjoying Castiel’s hole moving up and down on his hard cock. The high of it was glorious and Castiel mentally basked in it.

Years of fucking and bottoming constantly had it where Castiel had become _very_ good at sex. If only their university offered a program in bottoming because Castiel would already be on his way to completing a doctorate. He had never received a complaint and had gotten nothing but filthy, satisfied comments on what an enjoyable fuck he was.

Castiel bounced himself up and down on Dean’s cock, grinding down and working his hips quicker and quicker, as he chased his orgasm. He could feel it twisting in his gut, curling low in his body, as his breathing hitched and his cheeks flushed darker.

It was so easy to lose himself to the pleasure of fucking himself down on a thick cock. He adjusted his angle and pace to nail his prostate, pleasure bursting bright and hot inside of him, as he dragged himself closer and closer to release.

Under him Dean was jerking, swearing and wordlessly begging into his gag for release.

Castiel stared down at Dean’s red face, at the desperation in lust dark eyes, as he moved quicker and quicker. He was sure he looked wrecked, mouth open and eyes hooded, as his body moved at an uneven pace the closer he got to his orgasm.

It took the tiniest of touches to have his entire body seizing up, ass clamping viciously down on Dean’s hard cock, as he came with a loud and echoing wail of pleasure. His hips idly moved as he stroked himself through it, dragging out his pleasure, as his release ended up all over Dean. Come landed on Dean’s chest, neck and face when Castiel had finished.

He could feel how Dean strained under him, pushing his hard cock deep into Castiel’s ass, as he yanked at his restraints no doubt wanting to grip Castiel so he could fuck until he came.

Castiel sighed in satisfaction, resting on top of Dean for a few more moments, before he slid off and Dean’s lube wet cock fell out of his ass causing his roommate to whimper. “That looks painful.” Castiel’s voice was rough from his pleasure. He reached out and stroked his finger lightly up the underside of Dean’s cock. “Does it hurt?” he asked with faux concern.

Dean nodded jerkily, eyes wild and need clear as day on his face.

Castiel frowned in thought. “I don’t see what everyone was moaning so loudly about.” He could see shocked realization filling Dean’s eyes. “I mean…it was _good_ but it _wasn’t_ _great_.” Castiel scrunched his face up, “Maybe, if you’re lucky, I’ll let you try again and if you actually give me something to brag about I’ll let you fuck and come in my slutty cocksucking mouth.”

He leaned down and slowly let his tongue brush over the head of Dean’s purpling cock. It had Dean jolting violently and moaning in pain at the denial of release.

Dean’s phone went off.

Castiel blinked before leaning over to pick it up. He grinned. “Looks like you’ve got someone to help you with that little problem.” Castiel idly stroked Dean’s hard cock as he responded to whoever Samandriel was. He let one of Dean’s ‘booty calls’, it was more than obvious by the content of the text messages, know that Dean would be all ready for him to ride into the mattress before he placed the phone down. Dean’s phone beeped within seconds. He checked the text and left the phone on the bed this time. “Samandriel is _very_ excited to help you.”

He slid off Dean’s bed, gathered his things and headed towards Dean’s bedroom door.

“Have fun. Next time give me a reason to be impressed. I’ve had men in their fifties leave me far more satisfied.” One of them _might_ have been his home town’s perverted Mayor but Castiel wasn’t planning on standing there and bragging about it. He gave Dean a look of disappointment. “Maybe a second time will do it? Get some practice in before you try again.” The door shut behind him, Dean’s muffled shouts causing him to snicker, as he headed back towards his room.

Castiel slicked his hole up, pushed a plug in and dragged on clothing before heading towards the door with his keys and wallet. He opened it just in time to see a fresh faced, bright eyed guy who looked exactly like Dean’s type of bottom.

“He’s in his room. I just finished getting him ready for you.” Castiel watched those eyes widen, “Apparently he wanted to try something new.” He shrugged it off as though it was nothing and Samandriel seemed to except it without comment. “Have fun!”

“Oh I will.” The tone was practically dreamy, “Dean is amazing in bed. My friend was the one who suggested I should give him a try.” Samandriel was already toeing off his shoes and heading in the direction of Dean’s room with a bounce in his step. Castiel shook his head. That was probably one of Dean’s fuck buddies who had kept him up all night when he was trying to sleep. It seemed like people were making fucking recommendations.

Castiel locked the door behind him and headed down the hallway. He was looking for someone older, someone more experienced, to bring back and have fuck him through the mattress where Dean could _hear_ exactly how much fun Castiel was having with a cock fucking him that _wasn’t_ Dean’s.

First, though, he was spending a few hours in a gloryhole.

**Notes for the Chapter:**

> After receiving so many delightful comments on the first chapter I thought you all might enjoy a second one. Plus I thought you all might enjoy a lighter but still kinky fic with bottom!Cas.
> 
> I really do hope that you enjoyed this addition and the progression of this particular story.
> 
> Please leave a comment and let me know what you thought. Remember comments are motivation for continuing to write and post fanfics!

**Author's Note:**

> Figured I would put a bottom!Cas fic out as well since my 400th fic was a long fic with all kinds of bottom!Dean. Hopefully my bottom!Cas readers liked this one!!
> 
> I thought I would thank all of my readers and those sweet people who have left me all kinds of lovely comments on my fics. At 401 I've written an interesting variety and I hope people have found at least a couple of my fics that they enjoyed. Again I'm still going through that folder on my laptop though I keep getting a bit distracted so this is getting dragged out a bit. This fic is another one that was waiting to be finished, fixed and posted.
> 
>  
> 
> Please leave a comment and let me know what you thought. Remember comments are motivation for continuing to write and post fanfics!


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